2,2-Dimethyl-1,3-dioxane-4,6-dione → 7,8-Dimethoxy-3-carboxy-coumarin

HRID 240032Notes

Reaction equation

HRID 240032 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:5]([CH:6]=O)[C:4]=1[OH:13].CC1(C)O[C:20](=[O:21])[CH2:19][C:17](=[O:18])[O:16]1>O>[CH3:12][O:11][C:10]1[C:3]([O:2][CH3:1])=[C:4]2[C:5]([CH:6]=[C:19]([C:17]([OH:18])=[O:16])[C:20](=[O:21])[O:13]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 879993,4-Dimethoxysalicylaldehyde

Product 1

HCID 149549637,8-Dimethoxy-3-carboxy-coumarinYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

3,4-dimethoxy-salicylaldehyde (252.8 mg, 1.39 mmol) and Meldrum's acid (200 mg, 1.39 mmol) were combined in H2O (2 mL). The solution was stirred at 75° C. for 2 h. After cooling to room temperature, the precipitate was filtered and dried at suction to give 271.0 mg of 7,8-dimethoxy-3-carboxy-coumarin in an 78% yield.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was filtered
  3. customdried at suction

Sources & evidence

ORD record
ord-1c1d151adb9e46e2b8b59c4bd1951d8d
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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